WO2022055169A1 - Composé pour élément optoélectronique organique, composition pour élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage - Google Patents

Composé pour élément optoélectronique organique, composition pour élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage Download PDF

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Publication number
WO2022055169A1
WO2022055169A1 PCT/KR2021/011732 KR2021011732W WO2022055169A1 WO 2022055169 A1 WO2022055169 A1 WO 2022055169A1 KR 2021011732 W KR2021011732 W KR 2021011732W WO 2022055169 A1 WO2022055169 A1 WO 2022055169A1
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group
substituted
unsubstituted
formula
compound
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PCT/KR2021/011732
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English (en)
Korean (ko)
Inventor
이병관
이윤만
신선웅
이상신
장기포
남궁란
박승인
정성현
정호국
조영경
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삼성에스디아이 주식회사
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Priority to CN202180040437.6A priority Critical patent/CN115916760A/zh
Priority to US17/924,486 priority patent/US20230183190A1/en
Priority to JP2023515653A priority patent/JP2023542848A/ja
Priority to EP21867035.4A priority patent/EP4212517A1/fr
Publication of WO2022055169A1 publication Critical patent/WO2022055169A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/301—Details of OLEDs
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • An organic optoelectronic diode is a device capable of converting electrical energy and optical energy.
  • Another embodiment provides a display device including the organic optoelectronic device.
  • a compound for an organic optoelectronic device represented by the following formula (1).
  • the first compound may be the compound for an organic optoelectronic device described above, and the second compound may be represented by the following Chemical Formula 2.
  • A is any one selected from the rings listed in Group II and Group III,
  • At least one of R11 to R14 and R15 to R21 is a group represented by the following formula (a),
  • L1 to L3 are each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,
  • L1 to L3 may each independently be a single bond or a substituted or unsubstituted phenylene group.
  • At least one of R11 to R14 and R15 to R21 is a group represented by the following formula (a),
  • X1 may be CRgRh or SiRiRj, and X2 may be O or S.
  • L5 and L6 may each independently represent a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
  • Ar3 and Ar4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, A substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or It may be an unsubstituted benzofuranofluorenyl group, or a substituted or unsubstituted benzothiophenefluorenyl group.
  • the emission layer 130 may include, for example, the above-described first compound for an organic optoelectronic device and the second compound for an organic optoelectronic device, respectively, as a phosphorescent host.
  • Another embodiment of the present invention may be an organic light emitting device including an electron transport region 150 in addition to the light emitting layer 130 as the organic layer 105 as shown in FIG. 3 .
  • the luminance was measured at that time using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and results were obtained.
  • the devices of Examples 1 to 12 and Comparative Examples 1 to 5 emit light with an initial luminance (cd/m2) of 6,000 cd/m2 using the Polaronics lifetime measurement system, and By measuring the decrease in luminance, the time at which the luminance decreased to 95% compared to the initial luminance was measured as the T95 lifetime.

Abstract

La présente invention concerne un composé pour un élément optoélectronique organique, représenté par la formule chimique 1, une composition pour un élément optoélectronique organique, la composition comprenant le composé, un élément optoélectronique organique et un dispositif d'affichage. La description de la formule chimique 1 est telle que définie dans le mémoire descriptif.
PCT/KR2021/011732 2020-09-09 2021-09-01 Composé pour élément optoélectronique organique, composition pour élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage WO2022055169A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN202180040437.6A CN115916760A (zh) 2020-09-09 2021-09-01 用于有机光电元件的化合物、用于有机光电元件的组成物、有机光电元件及显示装置
US17/924,486 US20230183190A1 (en) 2020-09-09 2021-09-01 Compound for organic optoelectronic element, composition for organic optoelectronic element, organic optoelectronic element, and display device
JP2023515653A JP2023542848A (ja) 2020-09-09 2021-09-01 有機光電子素子用化合物、有機光電子素子用組成物、有機光電子素子および表示装置
EP21867035.4A EP4212517A1 (fr) 2020-09-09 2021-09-01 Composé pour élément optoélectronique organique, composition pour élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020200115635A KR20220033348A (ko) 2020-09-09 2020-09-09 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
KR10-2020-0115635 2020-09-09

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WO2022055169A1 true WO2022055169A1 (fr) 2022-03-17

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PCT/KR2021/011732 WO2022055169A1 (fr) 2020-09-09 2021-09-01 Composé pour élément optoélectronique organique, composition pour élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage

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US (1) US20230183190A1 (fr)
EP (1) EP4212517A1 (fr)
JP (1) JP2023542848A (fr)
KR (1) KR20220033348A (fr)
CN (1) CN115916760A (fr)
TW (1) TWI773513B (fr)
WO (1) WO2022055169A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114560844A (zh) * 2022-04-28 2022-05-31 浙江华显光电科技有限公司 N杂芳香衍生物、有机发光器件、显示面板和显示装置

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5061569A (en) 1990-07-26 1991-10-29 Eastman Kodak Company Electroluminescent device with organic electroluminescent medium
JPH059471A (ja) 1991-07-03 1993-01-19 Mitsui Toatsu Chem Inc 有機電界発光素子
WO1995009147A1 (fr) 1993-09-29 1995-04-06 Idemitsu Kosan Co., Ltd. Element electroluminescent organique et derive d'arylenediamine
JPH07126615A (ja) 1993-11-01 1995-05-16 Matsushita Electric Ind Co Ltd 電界発光素子
JPH1095973A (ja) 1996-07-24 1998-04-14 Mitsui Petrochem Ind Ltd 走行制御用発光性化合物及び該化合物を用いた走行制御方法
JP2010138121A (ja) * 2008-12-12 2010-06-24 Canon Inc トリアジン化合物及びこれを用いた有機発光素子
KR101423173B1 (ko) 2010-11-04 2014-07-25 제일모직 주식회사 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
KR20170096770A (ko) * 2016-02-17 2017-08-25 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN108586188A (zh) * 2018-06-01 2018-09-28 石家庄诚志永华显示材料有限公司 *衍生物、包含该*衍生物的材料和有机电致发光器件
KR20190007789A (ko) * 2017-07-13 2019-01-23 에스에프씨 주식회사 고효율 및 장수명 특성을 가지는 유기 발광 소자
KR20190103765A (ko) * 2018-02-28 2019-09-05 주식회사 엘지화학 유기 발광 소자

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KR20150126526A (ko) * 2014-05-02 2015-11-12 삼성디스플레이 주식회사 유기 발광 소자
KR102464552B1 (ko) * 2015-01-29 2022-11-08 엘지디스플레이 주식회사 적색 인광 호스트 화합물 및 그를 이용한 유기 발광 소자와 디스플레이 장치
JP7135536B2 (ja) * 2018-07-25 2022-09-13 東ソー株式会社 縮合環化合物
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5061569A (en) 1990-07-26 1991-10-29 Eastman Kodak Company Electroluminescent device with organic electroluminescent medium
JPH059471A (ja) 1991-07-03 1993-01-19 Mitsui Toatsu Chem Inc 有機電界発光素子
WO1995009147A1 (fr) 1993-09-29 1995-04-06 Idemitsu Kosan Co., Ltd. Element electroluminescent organique et derive d'arylenediamine
JPH07126615A (ja) 1993-11-01 1995-05-16 Matsushita Electric Ind Co Ltd 電界発光素子
JPH1095973A (ja) 1996-07-24 1998-04-14 Mitsui Petrochem Ind Ltd 走行制御用発光性化合物及び該化合物を用いた走行制御方法
JP2010138121A (ja) * 2008-12-12 2010-06-24 Canon Inc トリアジン化合物及びこれを用いた有機発光素子
KR101423173B1 (ko) 2010-11-04 2014-07-25 제일모직 주식회사 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
KR20170096770A (ko) * 2016-02-17 2017-08-25 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20190007789A (ko) * 2017-07-13 2019-01-23 에스에프씨 주식회사 고효율 및 장수명 특성을 가지는 유기 발광 소자
KR20190103765A (ko) * 2018-02-28 2019-09-05 주식회사 엘지화학 유기 발광 소자
CN108586188A (zh) * 2018-06-01 2018-09-28 石家庄诚志永华显示材料有限公司 *衍生物、包含该*衍生物的材料和有机电致发光器件

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Title
TETRAHEDRON LETTERS, no. 27, 2006, pages 4581 - 4584

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114560844A (zh) * 2022-04-28 2022-05-31 浙江华显光电科技有限公司 N杂芳香衍生物、有机发光器件、显示面板和显示装置
CN114560844B (zh) * 2022-04-28 2022-08-16 浙江华显光电科技有限公司 N杂芳香衍生物、有机发光器件、显示面板和显示装置

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KR20220033348A (ko) 2022-03-16
EP4212517A1 (fr) 2023-07-19
TW202210614A (zh) 2022-03-16
JP2023542848A (ja) 2023-10-12
TWI773513B (zh) 2022-08-01
US20230183190A1 (en) 2023-06-15
CN115916760A (zh) 2023-04-04

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